Trifluoroacetic acid → 6-bromo-4-(((3R,4R)-3-ethylpiperidin-4-yl)amino)pyrrolo[1,2-b]pyridazine-3-carboxamide

HRID 877753ノート

反応式

HRID 877753 の反応式
[Br:1][C:2]1[CH:3]=[C:4]2[C:9]([NH:10][C@@H:11]3[CH2:16][CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13][C@H:12]3[CH2:24][CH3:25])=[C:8]([C:26](=[O:28])[NH2:27])[CH:7]=[N:6][N:5]2[CH:29]=1.FC(F)(F)C(O)=O>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]2[C:9]([NH:10][C@@H:11]3[CH2:16][CH2:15][NH:14][CH2:13][C@H:12]3[CH2:24][CH3:25])=[C:8]([C:26]([NH2:27])=[O:28])[CH:7]=[N:6][N:5]2[CH:29]=1

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 68291228(3R,4R)-tert-butyl 4-((6-bromo-3-carbamoylpyrrolo[1,2-b]pyridazin-4-yl)amino)-3-ethylpiperidine-1-carboxylate

生成物 1

HCID 682916696-bromo-4-(((3R,4R)-3-ethylpiperidin-4-yl)amino)pyrrolo[1,2-b]pyridazine-3-carboxamide収率 100%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of (3R,4R)-tert-butyl 4-((6-bromo-3-carbamoylpyrrolo[1,2-b]pyridazin-4-yl)amino)-3-ethylpiperidine-1-carboxylate (350 mg, 0.750 mmol) in dichloromethane (3.8 ml) cooled to 0° C. was added trifluoroacetic acid (578 μl, 7.50 mmol). The reaction was allowed to warm to room temperature and stirring was continued for 1 hr. After removal of the solvent, the residue was taken into ethyl acetate, washed successively with saturated sodium bicarbonate, water, and brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure, yielding 6-bromo-4-(((3R,4R)-3-ethylpiperidin-4-yl)amino)pyrrolo[1,2-b]pyridazine-3-carboxamide (275 mg, 0.75 mmol, 100% yield) as a yellow solid. LCMS (Method K) m/z 368.3 ([M+H]+). Analytical SFC conditions, Column: CC4 from ES Industries; Mobile phase: 10-50% MeOH (with 0.1% DEA) in CO2 in 8 min, 50% MeOH (with 0.1% DEA) in CO2 for 4 more min; Temperature: 40° C., Flow rate: 3 mL/min, BPR: 140 bars, Detection: UV (254 & 220 nm). Retention Time (min): 8.153 (>98.5% ee).

後処理

  1. customAfter removal of the solvent
  2. washwashed successively with saturated sodium bicarbonate, water, and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-76cd9a58fabe4fb19c793608cc77fc3d
出典データセット
uspto-grants-2015_03
特許番号
US08987268B2

反応ノート

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